4-Methoxybenzoic Acid → 4-Methoxy-3-(morpholine-4-sulfonyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

p-Anisic acid (25.6 g, 168 mmol) was added neat to stirring chlorosulfonic acid (40 mL). This reaction was heated to 65° C. for 4 hours. The solution was poured very slowly into 500 mL of crushed ice, which was itself placed in a dry-ice/acetone bath to keep it cool. The water suspension that formed was allowed to stir for one hour, and it was then filtered. The solid was suspended in ether/dichloromethane (200 mL of 50/50), and excess morpholine (29 mL, 333 mmol) was added slowly. An immediate reaction occurred, but the reaction was allowed to stir overnight and then filtered and dried to provide the title compound (35 g, 69%). 1HNMR (DMSO-d6) δ13.2 (bs, 1H), 8.29 (d, J=2 Hz, 1H), 8.28 (dd, J=9 Hz, 2 Hz, 1H), 7.40 (d, J=9 Hz, 1H), 3.99 (s, 3H), 3.60 (m, 4H), 3.10 (m, 4H). MS (ES-POS): [M−H]=300.

Provenance & Evidence